874660-40-9

Upstream product

• 142561-89-5 (R)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol 
• 289619-05-2 (S)-4-Benzyl-3-[(R)-2-(4-methoxy-benzyloxy)-pent-4-enoyl]-oxazolidin-2-one 
• 760181-72-4 (R)-2-(4-methoxybenzyloxy)pent-4-en-1-ol 

Downstream Products

• 874660-17-0 3-hydroxy-4-(4-methoxy-benzyloxy)-hept-6-enoic acid tert-butyl ester 
• 760181-72-4 (R)-2-(4-methoxybenzyloxy)pent-4-en-1-ol 
• 625-31-0 (S)-4-penten-2-ol 
• 874660-44-3 (S)-3-{(R)-3-Benzyloxy-2-[(1S,2R)-2-(4-methoxy-benzyloxy)-1-methyl-1-(2-triisopropylsilanyloxy-ethyl)-pent-4-enyloxy]-propionyl}-4-isopropyl-oxazolidin-2-one 
• 874660-46-5 (R)-5-Benzyloxy-4-[(1S,2R)-2-(4-methoxy-benzyloxy)-1-methyl-1-(2-triisopropylsilanyloxy-ethyl)-pent-4-enyloxy]-pent-1-en-3-ol 
• 874660-21-6 (S)-4-Isopropyl-3-{2-[(1S,2R)-2-(4-methoxy-benzyloxy)-1-methyl-1-(2-triisopropylsilanyloxy-ethyl)-pent-4-enyloxy]-acetyl}-oxazolidin-2-one 
• 874660-22-7 (S)-3-Benzyloxy-2-[(1S,2R)-2-(4-methoxy-benzyloxy)-1-methyl-1-(2-triisopropylsilanyloxy-ethyl)-pent-4-enyloxy]-propan-1-ol 
• 874660-45-4 (R)-3-Benzyloxy-2-[(1S,2R)-2-(4-methoxy-benzyloxy)-1-methyl-1-(2-triisopropylsilanyloxy-ethyl)-pent-4-enyloxy]-propionaldehyde 
• 874660-43-2 [(1S,2R)-2-(4-Methoxy-benzyloxy)-1-methyl-1-(2-triisopropylsilanyloxy-ethyl)-pent-4-enyloxy]-acetic acid 
• 874660-20-5 (3S,4R)-4-(4-Methoxy-benzyloxy)-3-methyl-1-triisopropylsilanyloxy-hept-6-en-3-ol 
• 874660-42-1 (R)-4-(4-Methoxy-benzyloxy)-1-triisopropylsilanyloxy-hept-6-en-3-one 
• 874660-19-2 (R)-4-(4-Methoxy-benzyloxy)-1-triisopropylsilanyloxy-hept-6-en-3-ol 
• 874660-41-0 (R)-4-(4-Methoxy-benzyloxy)-hept-6-ene-1,3-diol 
• 760181-73-5 (3R,4R)-4-(4-Methoxy-benzyloxy)-hept-6-en-3-ol 

Relevant academic research and scientific papers

Total synthesis of (–)-cephalosporolide D

In this communication, a concise and efficient synthetic route for the synthesis of (–)-Cephalosporolide D in enantioselective way has been described. In this synthesis, Mitsunobu esterification and Ring Closing Metathesis (RCM) for macrocyclic ring formation have been applied as key steps.

Enantioselective total synthesis of brevetoxin A: Unified strategy for the B, E, G, and J subunits

Brevetoxin A is a decacyclic ladder toxin that possesses 5-, 6-, 7-, 8-, and 9-membered oxacycles, as well as 22 tetrahedral stereocenters. Herein, we describe a unified approach to the B, E, G, and J rings based upon a ring-closing metathesis strategy from the corresponding dienes. The enolate technologies developed in our laboratory allowed access to the precursor acyclic dienes for the B, E, and G medium-ring ethers. The strategies developed for the syntheses of these four monocycles ultimately provided multigram quantities of each of the rings, supporting our efforts toward the completion of a convergent synthesis of brevetoxin A.

Convergent, stereoselective synthesis of the GHIJ fragment of brevetoxin A

(Chemical Equation Presented) A stereoselective synthesis of the GHIJ fragment of brevetoxin A utilizing a convergent assembly strategy is described. Glycolate alkylation, ring-closing metathesis, and Hosomi-Sakurai reactions were central operations in the construction of the G ring and J ring subunits, which were united through a Horner-Wadsworth-Emmons coupling. Subsequent dehydrative cyclization produced an endocyclic enol ether that was further elaborated to the tetracyclic GHIJ fragment of brevetoxin A.

A new approach to the synthesis of cyclic ethers via the intermolecular allylation of α-acetoxy ethers and ring-closing metathesis

A concise synthesis of the isolaurepinnacin skeleton 6 was achieved via the intermolecular allylation of the α-acetoxy ether 3 followed by ring-closing metathesis. This methodology was successfully applied to the convergent synthesis of the oxocene 15, an advanced synthetic intermediate for the total synthesis of laurencin.